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  • Writer's pictureBethany Crystal

Invite me out for coffee. Please.

  1. Say hello; express extreme excitement to see me.

  2. Tell me all about your last IRL business interaction, the last time you commuted, or some crazy thing you saw on the way here.

  3. Tell me again how weird it is to be doing anything in person.

  4. Ask me a series of rapidfire questions to recalibrate how you know me and jog your memory about the things important to me in my life. If you want to get fancy about it, the trick would be to ask in a way that doesn’t make it obvious you’ve forgotten these things. But even if you did forget, I’ll forgive you. Example include:

  5. Where I live: “Where have you been living all of this time? Did you stay local?"

  6. Where I work: “How’s job stuff going?” (The key is to play it safe. Stay vague if you don’t know.

  7. If I have kids: “And the family? Anything new?”

  8. If I got COVID: “I hope you’ve stayed healthy throughout it all…”

  9. Round out the last five minutes or any unnatural pauses in conversation with this catch-all phrase: “Ugh, everything is just so weird right now.” (Note: Max of 4 uses in a 60-minute coffee date.) You don’t even need to memorize this. In fact, you can just keep looking down at your phone the whole time we’re talking and follow along. I won’t mind, I’ll be too busy wondering if the guy on the street carrying three FreshDirect bags full of cat food is about to throw his shoe at us. What’s your schedule like next week? Shall we pencil something in? I’m not even asking for pen. I’m super flexible. I’m only asking that -- on the off-chance that you do decide to go into the office -- you put me right at the top of your shortlist of people to call. I know it may seem like I’m sending you mixed messages. I know two years ago I asked you please, for the love of java, stop inviting me out for coffee. But those were simpler times. I was ignorant back then, didn’t know how good I had it, what with my 1,200+ coffee-related emails and triple-decker-stacked afternoons of back-to-back meetings. Compare that to today, when my heart skips a beat just seeing a promotional email from Starbucks. I’m not too proud to admit this: I still haven’t figured out my perfect French press pour. I’m jittery in the mornings and catatonic in the afternoons. So let’s just call things what we are and leave the caffeine stuff to the experts. Tell me what you need, and I’ll be there. Are you trying to get a job in VC? Or maybe you’re looking for some fundraising advice? Do you only want to meet with me on the off-chance that I’ll like you enough to introduce you to someone you really want to know? I can work with that. Or maybe it’s career advice you’re after. Let’s meet up so I can download your brain then refer you to one of approximately 50 different blog posts I’ve written on the topic. When’s the last time you negotiated your salary, how can I help? Are thinking about executive coaching and need a few referrals? Looking for an all star designer for your team? Help me help you by putting my rolodex to work. Remind me what it’s like to be needed. Do you think this all sounds a little crazy? Desperate, even? Well maybe like we should meet up and talk about it. How’s Thursday at 3?

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